Downstream synthetic route of 105627-79-0

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105627-79-0, Isoquinoline-5-sulfonyl chloride hydrochloride is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step A: 4-(Isoquinoline-5-sulfonyl)-[1,4]diazepane-1-carboxylic acid tert-butyl esterTo a stirred suspension of isoquinoline-5-sulfonylchloride hydrochloride (3.00 g, 11.4 mmol) in anhydrous methylene chloride (100 mL) was added tert-butyl 1-homopiperazine carboxylate (3.00 g, 15.0 mmol) and triethylamine (4.36 g, 43.1 mmol). The mixture was stirred for 3 h, evaporated to dryness, mixed with a saturated solution of sodium bicarbonate (100 mL) and extracted with ethyl acetate (80 mL¡Á2). The combined extracts were dried, filtered and evaporated to give an oil (4.45 g, 100%). LCMS (+APCI) m/z 392 (M+H).

105627-79-0, As the paragraph descriping shows that 105627-79-0 is playing an increasingly important role.

Reference£º
Patent; Alcon Research, Ltd.; US7867999; (2011); B1;,
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Some tips on 105627-79-0

105627-79-0, 105627-79-0 Isoquinoline-5-sulfonyl chloride hydrochloride 13116932, aisoquinoline compound, is more and more widely used in various fields.

105627-79-0, Isoquinoline-5-sulfonyl chloride hydrochloride is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The synthetic procedure of compound 3i was conducted according to the reported procedures.56,57 To a 100mL round-bottomed flask add 5-isoquinoline sulfonic acid (2.10g, 10mmol), 25mL thionyl chloride, 1mL dimethylformamide, the resulting mixture was refluxed for 2h. After that, SOCl2 was removed by rotary evaporation, the residue was suspended in CH2Cl2, filtered, and washed with CH2Cl2 (2¡Á25mL). The precipitate was collected and dried in vacuum to give crude crystalline isoquinoline-5-sulfonyl chloride hydrochloride, yield 85% (2.25g). To a 100mL round-bottomed flask add isoquinoline-5-sulfonyl chloride hydrochloride (2.0g, 7.6mmol) and 20mL ice-cold deionized water. The mixture was added slowly equimolar NaHCO3 (0.64g), the resulting solution was extracted twice with CH2Cl2 (2¡Á20mL). Organic layer was dried over anhydrous sodium sulfate and added dropwise to a 25mL CH2Cl2 solution of ethylenediamine (1.37g, 22.8mmol) at 0C. The reaction continued for 1h at room temperature, washed with deionized water to remove the excess ethylenediamine, and evaporated off. The residue was recrystallized from ethanol to give pure 3i, yield 55%,

105627-79-0, 105627-79-0 Isoquinoline-5-sulfonyl chloride hydrochloride 13116932, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Article; Jin, Feng; Gao, Dan; Wu, Qin; Liu, Feng; Chen, Yuzong; Tan, Chunyan; Jiang, Yuyang; Bioorganic and Medicinal Chemistry; vol. 21; 18; (2013); p. 5694 – 5706;,
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Analyzing the synthesis route of 105627-79-0

105627-79-0, The synthetic route of 105627-79-0 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.105627-79-0,Isoquinoline-5-sulfonyl chloride hydrochloride,as a common compound, the synthetic route is as follows.

To a solution of isoquinoline-5-sulfonyl chloride hydrochloride (930 mg) in THF (20 ml) were added DIPEA (2.2 eq.) and (S-methoxycarbonylmethyl-piperazine-1-carboxylic acid tert-butyl ester (1 eq.). The reaction mixture was stirred at room temperature overnight. The solvent was evaporated and the residue was taken in DCM. The DCM layer was washed with 1 N sodium carbonate and then, with brine. The organic layer was evaporated and the residue was purified by chromatography on C-18 (water/CH3CN 100/0 to 50/50) to afford the intermediate methyl ester as a white powder (66 % yield).

105627-79-0, The synthetic route of 105627-79-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; DEVGEN N.V.; WO2008/49919; (2008); A2;,
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Brief introduction of 105627-79-0

The synthetic route of 105627-79-0 has been constantly updated, and we look forward to future research findings.

105627-79-0, Isoquinoline-5-sulfonyl chloride hydrochloride is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 1 52.8 g of 5-isoquinolinesulfonyl chloride hydrochloride was dissolved in 200 ml of water and extracted with 300 ml of dichloromethane. The resultant aqueous layer was taken out and adjusted to pH 5 with a saturated aqueous sodium hydrogencarbonate solution, and subjected to extraction with 200 ml dichloromethane. Then, the dichloromethane layers were mixed together and added dropwise to a dichloromethane solution (300 ml) containing 24.4 g of ethanolamine over 30 minutes while cooling with ice. The precipitated crystal was subjected to filtration, washed successively with 300 ml of water and 200 ml of ethyl acetate, and dried under reduced pressure at 40 C, to thereby obtain 40.0 g of N-(2-hydroxyethyl)-5-isoquinolinesulfonamide (yield: 79 %)., 105627-79-0

The synthetic route of 105627-79-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Asahi Kasei Kogyo Kabushiki Kaisha; EP471841; (1992); A1;,
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New learning discoveries about 105627-79-0

105627-79-0, As the paragraph descriping shows that 105627-79-0 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.105627-79-0,Isoquinoline-5-sulfonyl chloride hydrochloride,as a common compound, the synthetic route is as follows.

2) In 1000 L in the reactor are separately put into dichloromethane 500 L, homopiperazine 50 kg and liquid ammonia 33 kg, stirring solution cleaning, adding step 1) obtained FZ010 – 1. In the 10 C insulation reaction to the TLC detection without FZ010 – 1 residue when the end of the reaction, the reaction time is 2 – 4 H-. The reaction […] purified water 300 L, stir, fully after standing, divide the methylene chloride level. The aqueous layer then 100 L methylene chloride extraction, repeating the extraction of two, then the collection of methylene chloride level; to-methylene chloride layer in purified water 300 L, dropwise 4 mol/L hydrochloric acid solution to adjust system for pH 4.5 – 5.0, during the dropping temperature of not higher than 40 C, layered; collecting water layer, mass fraction of 20% NaOH solution to adjust the pH of the aqueous layer to 8.0, during the dropping temperature of not higher than 40 C. For 200 L methylene chloride extraction, repeating the extraction of 3 times, then the collection of methylene chloride level, vacuum distillation, to obtain yellowish sticks the thick oil objects, about 21.8 kg, is the intermediate hexahydro -1 – (5 – isoquinoline sulfonyl) – 1 H – 1, 4 – benzodiazepine salt (formula (I) in the FZ010 – 2), yield is 54.5%.

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Reference£º
Patent; Henan Runhong Pharmaceutical Co., Ltd.; Cui Hailong; Ma Liyan; Wang Xiaoxue; Shi Yongzhi; An Xiaomin; Shi Huifeng; Zhang Wei; (8 pag.)CN109574992; (2019); A;,
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Downstream synthetic route of 105627-79-0

105627-79-0, As the paragraph descriping shows that 105627-79-0 is playing an increasingly important role.

105627-79-0, Isoquinoline-5-sulfonyl chloride hydrochloride is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 5 In 10 ml of ice water was dissolved 1.38 g of 5-isoquinolinesulfonyl chloride hydrochloride as obtained in Reference Example. Then, the pH of the solution was adjusted to 6 with an aqueous sodium hydrogencarbonate solution, followed by extraction with 30 ml of dichloromethane. The dichloromethane layer was added dropwise to a 20 ml of dichloromethane solution containing 0.85 g of 1-methylhomopiperazine and 1.0 g of triethylamine while cooling with ice The mixture was stirred at a temperature of 10 C to 20 C for 2 hours, washed with water, and dried with anhydrous magnesium sulfate. Then, the dichloromethane was removed under reduced pressure to obtain an oily residue. The thus obtained oily residue was subjected to purification by the silica gel column chromatography (Wacogel C-200, 80 g; solvent: a 3 % methanol solution in chloroform), thereby to obtain 1.25 g of 1-(5-isoquinolinesulfonyl)-4-methylhomopiperazine, i.e., Compound (18) in a 86 % yield. Analytical data on Compound (18) are given below. Substantially the same procedures as described above were repeated except that each of the compounds of the formula (IV) as set forth in Table 2-1 was used in place of 1-methylhomopiperazine used above and that other reaction conditions were changed as indicated in Table 2-1. As a result, there were obtained 1-(5-isoquinolinesulfonyl)-4-ethylhomopiperazine, i.e., Compound (19); 1-(5-isoquinolinesulfonyl)-4-butylhomopiperazine,i.e.,Compound (21); 1-(5-isoquinolinesulfonyl)-4-hexylhomopiperazine,i.e.,Compound (22). The yields and analytical values of these compounds are shown in Table 2-2.

105627-79-0, As the paragraph descriping shows that 105627-79-0 is playing an increasingly important role.

Reference£º
Patent; Asahi Kasei Kogyo Kabushiki Kaisha; Hidaka, Hiroyoshi; EP187371; (1991); B1;,
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Analyzing the synthesis route of 105627-79-0

105627-79-0, The synthetic route of 105627-79-0 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.105627-79-0,Isoquinoline-5-sulfonyl chloride hydrochloride,as a common compound, the synthetic route is as follows.

Powdered isoquinoline-5-sulfonyl chloride hydrochloride (1.00 g, 3.79 mmol) is added in small portions to a stirred solution of tert-butylamine (2.00 mL, 18.9 mmol) in CHIC12 (10 mL) at 0 C under nitrogen. The resultant mixture is allowed to stir at ambient temperature for 1 hour. Ethyl acetate (50 mL) is added to the mixture and the mixture is washed with saturated aqueous NAHCO3 (20 mL). The organic layer is dried over MGS04, filtered and concentrated. The crude product is chromatographed on silica (gradient 0-2% CH30H in CH2C12) to give 857 mg (3.24 mmol, 86% yield) of the title compound as a white solid. ESIMS : m/z 265 (M+H) +. Analysis for C13HL6N202S : calcd : C, 59.07 ; H, 6.10 ; N, 10.60 ; found: C, 59.21 ; H, 6.01 ; N, 10.67.

105627-79-0, The synthetic route of 105627-79-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ELI LILLY AND COMPANY; WO2004/94386; (2004); A1;,
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Analyzing the synthesis route of 105627-79-0

The synthetic route of 105627-79-0 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.105627-79-0,Isoquinoline-5-sulfonyl chloride hydrochloride,as a common compound, the synthetic route is as follows.

EXAMPLE 17 In 100 ml of ice water was dissolved 8.8 g of 5-isoquinolinesulfonyl chloride hydrochloride, and the pH of the solution was adjusted to 6 with a saturated aqueous sodium hydrogencarbonate solution, followed by extraction with 100 ml of dichloromethane. The dichloromethane layer was added dropwise to a 100mml of dichloromethane solution containing 5.30 g of N-hexyl-2-hydroxypropylamine and 4.0 g of triethylamine over a period of 20 minutes while cooling with ice. The mixture was stirred at a temperature of 15 C. to 20 C. for 2 hours, washed with water, and dried with anhydrous magnesium sulfate. Then, the dichloromethane was removed under reduced pressure to obtain an oily residue. The thus obtained oily residue was subjected to purification by silica gel column chromatography (Wacogel C-200, 200 g; solvent: a 2% methanol solution in chloroform) to obtain 9.02 g of N-hexyl-N-(2-hydroxypropyl)-5-isoquinolinesulfonamide., 105627-79-0

The synthetic route of 105627-79-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Asahi Kasei Kogyo Kabushiki Kaisha; US4798897; (1989); A;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

 

Analyzing the synthesis route of 105627-79-0

105627-79-0, The synthetic route of 105627-79-0 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.105627-79-0,Isoquinoline-5-sulfonyl chloride hydrochloride,as a common compound, the synthetic route is as follows.

Reference Preparation Example Homopiperazine (3.413 g) was dissolved in tetrahydrofuran (57 ml) with stirring. After cooling the solution to -5 C, 5-isoquinolinesulfonyl chloride hydrochloride (3.00 g) was added while maintaining the intemal temperature at 10 C or less. The mixture was stirred at 5 C or less for four hours. The reaction mixture was allowed to stand to reach room temperature and filtered to remove insoluble matter. The filtrate was concentrated under reduced pressure, followed by the addition of ethyl acetate (57 ml), water (17 ml), and 3 N hydrochloric acid aqueous solution (6.4 ml). The mixture was separated into layers to obtain a water layer. After washing the water layer with ethyl acetate (7 ml), water (6 ml), ethyl acetate (57 ml), and 6 N sodium hydroxide aqueous solution (3 ml) were added to separate the mixture into layers and obtain an organic layer. The organic layer was concentrated under reduced pressure and the residue was dried under reduced pressure to obtain fasudil (1.36 g). The yield was 41%. The fasudil is processed by the method described in JP-A-9-71582 to obtain fasudil hydrochloride. Fasudil can also be obtained in the same manner using the solvents listed below instead of tetrahydrofuran used in the Reference Preparation Example at yields described in the parentheses. Acetone (22%), acetonitrile (30%), 1,2-dimethoxyethane (31%), 2-butanone (24%), anisole (34%), isopropyl ether (10%), ethyl acetate (38%), toluene (18%), etc. Concentration of the filtrate was unnecessary when anisole, isopropyl ether, ethyl acetate, and toluene were used as the solvent.

105627-79-0, The synthetic route of 105627-79-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Asahi Kasei Pharma Corporation; EP1726306; (2006); A1;,
Isoquinoline – Wikipedia
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New learning discoveries about 105627-79-0

105627-79-0, As the paragraph descriping shows that 105627-79-0 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.105627-79-0,Isoquinoline-5-sulfonyl chloride hydrochloride,as a common compound, the synthetic route is as follows.

EXAMPLE 1 52.8 g of 5-isoquinolinesulfonyl chloride hydrochloride was dissolved in 200 ml of water and extracted with 300 ml of dichloromethane. The resultant aqueous layer was taken out and adjusted to pH 5 with a saturated aqueous sodium hydrogencarbonate solution, and subjected to extraction with 200 ml dichloromethane. Then, the dichloromethane layers were mixed together and added dropwise to a dichloromethane solution (300 ml) containing 24.4 g of ethanolamine over 30 minutes while cooling with ice. The precipitated crystal was subjected to filtration, washed successively with 300 ml of water and 200 ml of ethyl acetate, and dried under reduced pressure at 40 C., to thereby obtain 40.0 g of N-(2-hydroxyethyl)-5-isoquinolinesulfonamide (yield: 79%).

105627-79-0, As the paragraph descriping shows that 105627-79-0 is playing an increasingly important role.

Reference£º
Patent; Asahi Kasei Kogyo Kabushiki Kaisha; US5340811; (1994); A;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem